NO340621B1 - Azaindazolforbindelser, farmasøytiske preparater derav og anvendelse derav - Google Patents

Info

Publication number

NO340621B1

NO340621B1 NO20080408A NO20080408A NO340621B1 NO 340621 B1 NO340621 B1 NO 340621B1 NO 20080408 A NO20080408 A NO 20080408A NO 20080408 A NO20080408 A NO 20080408A NO 340621 B1 NO340621 B1 NO 340621B1

Authority

NO

Norway

Prior art keywords

group

nhr

nhc

alkyl

independently selected

Prior art date

2005-06-22

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• 239000000825 pharmaceutical preparation Substances 0.000 title claims description 17
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical class C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 title description 9
• 150000001875 compounds Chemical class 0.000 claims description 227
• 229910052739 hydrogen Inorganic materials 0.000 claims description 132
• 239000001257 hydrogen Substances 0.000 claims description 127
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 98
• 125000001424 substituent group Chemical group 0.000 claims description 80
• 229910052736 halogen Inorganic materials 0.000 claims description 77
• 150000002367 halogens Chemical class 0.000 claims description 75
• 150000002431 hydrogen Chemical class 0.000 claims description 75
• 238000002360 preparation method Methods 0.000 claims description 68
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 67
• -1 C1-5-haloalkyl Chemical group 0.000 claims description 63
• 125000003118 aryl group Chemical group 0.000 claims description 54
• 229910052757 nitrogen Inorganic materials 0.000 claims description 54
• 238000000034 method Methods 0.000 claims description 51
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 49
• 102100031172 C-C chemokine receptor type 1 Human genes 0.000 claims description 46
• 101710149814 C-C chemokine receptor type 1 Proteins 0.000 claims description 46
• 125000001072 heteroaryl group Chemical group 0.000 claims description 46
• 125000000217 alkyl group Chemical group 0.000 claims description 42
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 38
• 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims description 36
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 33
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 33
• 201000010099 disease Diseases 0.000 claims description 32
• 239000000460 chlorine Substances 0.000 claims description 28
• 125000001931 aliphatic group Chemical group 0.000 claims description 27
• 125000002971 oxazolyl group Chemical group 0.000 claims description 27
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 25
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 25
• 150000003839 salts Chemical class 0.000 claims description 25
• 125000004076 pyridyl group Chemical group 0.000 claims description 24
• 125000000335 thiazolyl group Chemical group 0.000 claims description 23
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• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 22
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• 125000005842 heteroatom Chemical group 0.000 claims description 20
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
• 229910052794 bromium Inorganic materials 0.000 claims description 19
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 18
• 150000001204 N-oxides Chemical class 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 17
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 17
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 16
• 125000002947 alkylene group Chemical group 0.000 claims description 15
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• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 13
• 239000003112 inhibitor Substances 0.000 claims description 13
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• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
• 229910052740 iodine Inorganic materials 0.000 claims description 12
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 11
• 210000000265 leukocyte Anatomy 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• 125000002757 morpholinyl group Chemical group 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 8
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• 230000005012 migration Effects 0.000 claims description 7
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• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
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• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 6
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
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• 125000001425 triazolyl group Chemical group 0.000 claims description 5
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• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
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• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
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• 125000002541 furyl group Chemical group 0.000 claims description 3
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• 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
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• 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 2
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• 206010016946 Food allergy Diseases 0.000 claims 1
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• 230000001419 dependent effect Effects 0.000 claims 1
• 201000002491 encephalomyelitis Diseases 0.000 claims 1
• 125000000623 heterocyclic group Chemical group 0.000 claims 1
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• 206010025135 lupus erythematosus Diseases 0.000 claims 1
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• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 274
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• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 137
• 235000019253 formic acid Nutrition 0.000 description 137
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 132
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